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A pirate of near-mythical reputation, the Dread Pirate Roberts is feared across the seven seas for his ruthlessness and swordfighting prowess, and is well known for taking no prisoners.

It is revealed during the course of the story that Roberts is not one man, but a series of individuals who pass the name and reputation to a chosen successor once they are wealthy enough to retire. When the time comes, "Roberts" and his chosen successor sail into port and discharge the crew. Then they hire a new crew, the ex-Roberts staying aboard as first mate and referring to his successor as "Captain Roberts". Once the crew grows accustomed to the new Roberts, the previous captain leaves to enjoy his retirement.

Westley, the hero of The Princess Bride, was on a voyage to seek his fortune when his ship was captured by the Dread Pirate (who never leaves captives alive) and Westley is reported dead.[2] While the other passengers are weeping and offering bribery for their lives, Westley simply asks Roberts to please not kill him. The "please" arousing his interest, Roberts asks, "Why should I make an exception of you?" Westley then explains his mission to get enough money to reunite with his true love, Buttercup. Westley's description of Buttercup's beauty moves Roberts to the point that he hires Westley as a personal attendant. While Roberts is impressed with Westley's work, he continues to keep Westley's future in doubt by saying each night, "Good night, Westley. Good work. Sleep well. I'll most likely kill you in the morning." After about three years, Roberts and Westley have grown close, and Roberts promotes Westley to his second-in-command. Shortly after that, Roberts reveals to Westley that the guise of the "Dread Pirate Roberts" is merely a pseudonym that he has inherited, and that his real name is Ryan. Roberts goes on to explain that the method works because Roberts' notorious reputation inspires overwhelming fear in sailors. Ships immediately capitulate and surrender their wealth rather than be captured, a fate they imagine to be certain death. A pirate operating under his own name is said to be incapable of such infamy: "No one would surrender to the Dread Pirate Westley." [3]

The fear inspired by the title is used in Westley's plan of invading the castle right before Buttercup's wedding. In the invasion the giant Fezzik poses as Roberts to inspire fear in the castle guard. The fear is amplified by Fezzik's size and a few more tricks, and it made the entire guard run away so that the invaders could enter with nearly no resistance.

In both the movie and the novel, Westley indicates that he plans to retire after reuniting with Buttercup. In the movie, he suggests that Inigo Montoya might succeed him. However, in the novel, no mention is made as to who is to succeed Westley as the Dread Pirate Roberts. In the first chapter of Buttercup's Baby (the supposed sequel to the novel), which is included in the 25th anniversary edition of the book, Goldman refers to 'Pierre', who is in charge of the pirate ship Revenge during Westley's absence and next in line to become the Dread Pirate Roberts. By the end of the chapter, Westley and his companions leave the ship again, presumably leaving Pierre once again in charge, but no mention is made of an official transfer of the title of Dread Pirate Roberts.

The creator (Ross William Ulbricht) of the Silk Road website used for illegal business transactions including buying and selling illicit drugs used Dread Pirate Roberts as a nickname. Just as in the story, the title can be passed down – another person is using the alias Dread Pirate Roberts, reopening the Silk Road website one month after the original site was seized by US law enforcement.[4]